Ranu, Brindaban C. ; Chattopadhyay, Kalicharan ; Banerjee, Subhash (2006) Indium(I) iodide promoted cleavage of diphenyl diselenide and disulfide and subsequent palladium(0)-catalyzed condensation with vinylic bromides. A simple one-pot synthesis of vinylic selenides and sulfides The Journal of Organic Chemistry, 71 (1). 423–425. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo052087i
Related URL: http://dx.doi.org/10.1021/jo052087i
Abstract
Diphenyl diselenide (and disulfide) undergo facile reaction with indium(I) iodide and the corresponding intermediate complex condenses in situ with a variety of substituted vinyl bromides in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium(0) [Pd(PPh3)4] in THF at room temperature to produce vinylic selenides and sulfides in good yields. The conversion of (E)-vinyl bromides is remarkably stereoselective giving (E)-vinyl selenides (and sulpfides) whereas the stereoselectivity in reaction of (Z)-vinyl bromides is not very good.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 41427 |
| Deposited On: | 30 May 2011 05:17 |
| Last Modified: | 30 May 2011 05:17 |
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